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Cheap flights from Santa Rosa to Chicago from $155

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Santa Rosa to Chicago departing on 8/25. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Santa Rosa to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Alaska Airlines Logo
6:13 am - 7:21 pmSTS  Santa Rosa Sonoma County-ORD Chicago O'Hare Intl
11h 08m1 stop San Diego
Alaska Airlines Logo
7:00 pm - 12:46 pmORD  Chicago O'Hare Intl-STS Santa Rosa Sonoma County
19h 46m1 stop Seattle/Tacoma Intl
$299Alaska Airlines
Sat, Sep 5 - Fri, Sep 11
Alaska Airlines Logo
6:13 am - 7:21 pmSTS  Santa Rosa Sonoma County-ORD Chicago O'Hare Intl
11h 08m1 stop San Diego
Alaska Airlines Logo
8:17 pm - 9:54 amORD  Chicago O'Hare Intl-STS Santa Rosa Sonoma County
15h 37m1 stop San Diego
$299Alaska Airlines
Sat, Sep 5 - Fri, Sep 11
Alaska Airlines Logo
6:16 am - 7:21 pmSTS  Santa Rosa Sonoma County-ORD Chicago O'Hare Intl
11h 05m1 stop San Diego
Alaska Airlines Logo
8:17 pm - 9:54 amORD  Chicago O'Hare Intl-STS Santa Rosa Sonoma County
15h 37m1 stop San Diego
$299Alaska Airlines
Sat, Sep 5 - Fri, Sep 11
American Airlines Logo
1:08 pm - 12:30 amSTS  Santa Rosa Sonoma County-ORD Chicago O'Hare Intl
9h 22m1 stop Phoenix Sky Harbor Intl
American Airlines Logo
5:00 am - 12:38 pmORD  Chicago O'Hare Intl-STS Santa Rosa Sonoma County
9h 38m1 stop Phoenix Sky Harbor Intl
$340American Airlines
Fri, Sep 11 - Mon, Sep 14
American Airlines Logo
1:08 pm - 10:31 pmSTS  Santa Rosa Sonoma County-ORD Chicago O'Hare Intl
7h 23m1 stop Phoenix Sky Harbor Intl
American Airlines Logo
5:00 am - 12:38 pmORD  Chicago O'Hare Intl-STS Santa Rosa Sonoma County
9h 38m1 stop Phoenix Sky Harbor Intl
$341American Airlines
Fri, Sep 11 - Wed, Sep 16
American Airlines Logo
1:08 pm - 12:30 amSTS  Santa Rosa Sonoma County-ORD Chicago O'Hare Intl
9h 22m1 stop Phoenix Sky Harbor Intl
American Airlines Logo
5:00 am - 12:09 pmORD  Chicago O'Hare Intl-STS Santa Rosa Sonoma County
9h 09m1 stop Dallas/Fort Worth
$345American Airlines
Thu, Sep 10 - Mon, Sep 14
Alaska Airlines Logo
10:34 am - 7:21 pmSTS  Santa Rosa Sonoma County-ORD Chicago O'Hare Intl
6h 47m1 stop San Diego
Alaska Airlines Logo
6:00 am - 12:46 pmORD  Chicago O'Hare Intl-STS Santa Rosa Sonoma County
8h 46m1 stop Seattle/Tacoma Intl
$365Alaska Airlines
Sun, Sep 6 - Wed, Sep 16
Alaska Airlines Logo
10:34 am - 7:21 pmSTS  Santa Rosa Sonoma County-ORD Chicago O'Hare Intl
6h 47m1 stop San Diego
Alaska Airlines Logo
4:08 pm - 9:59 pmORD  Chicago O'Hare Intl-STS Santa Rosa Sonoma County
7h 51m1 stop Seattle/Tacoma Intl
$365Alaska Airlines
Sun, Sep 6 - Sat, Sep 19
Alaska Airlines Logo
10:34 am - 7:21 pmSTS  Santa Rosa Sonoma County-ORD Chicago O'Hare Intl
6h 47m1 stop San Diego
Alaska Airlines Logo
2:22 pm - 8:59 pmORD  Chicago O'Hare Intl-STS Santa Rosa Sonoma County
8h 37m1 stop Portland
$365Alaska Airlines
Wed, Sep 9 - Fri, Sep 11
Alaska Airlines Logo
10:34 am - 7:21 pmSTS  Santa Rosa Sonoma County-ORD Chicago O'Hare Intl
6h 47m1 stop San Diego
Alaska Airlines Logo
3:52 pm - 9:59 pmORD  Chicago O'Hare Intl-STS Santa Rosa Sonoma County
8h 07m1 stop Seattle/Tacoma Intl
$365Alaska Airlines
Sun, Sep 6 - Tue, Sep 15

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American Airlines flights from Santa Rosa to Chicago

Our best American Airlines deals on Santa Rosa to Chicago flight tickets
American Airlines
Sep 11
STS1:08 pmSanta Rosa Sonoma County
9h 22m
1 stop
ORD12:30 amChicago O'Hare Intl
Sep 14
ORD5:00 amChicago O'Hare Intl
9h 38m
1 stop
STS12:38 pmSanta Rosa Sonoma County
$340
American Airlines
Sep 11
STS1:08 pmSanta Rosa Sonoma County
7h 23m
1 stop
ORD10:31 pmChicago O'Hare Intl
Sep 16
ORD5:00 amChicago O'Hare Intl
9h 38m
1 stop
STS12:38 pmSanta Rosa Sonoma County
$341
American Airlines
Sep 10
STS1:08 pmSanta Rosa Sonoma County
9h 22m
1 stop
ORD12:30 amChicago O'Hare Intl
Sep 14
ORD5:00 amChicago O'Hare Intl
9h 09m
1 stop
STS12:09 pmSanta Rosa Sonoma County
$345

Alaska Airlines flights from Santa Rosa to Chicago

Our best Alaska Airlines deals on Santa Rosa to Chicago flight tickets
Alaska Airlines
Sep 5
STS6:13 amSanta Rosa Sonoma County
11h 08m
1 stop
ORD7:21 pmChicago O'Hare Intl
Sep 11
ORD8:17 pmChicago O'Hare Intl
15h 37m
1 stop
STS9:54 amSanta Rosa Sonoma County
$299
Alaska Airlines
Sep 6
STS10:34 amSanta Rosa Sonoma County
6h 47m
1 stop
ORD7:21 pmChicago O'Hare Intl
Sep 16
ORD6:00 amChicago O'Hare Intl
8h 46m
1 stop
STS12:46 pmSanta Rosa Sonoma County
$365
Alaska Airlines
Sep 6
STS10:34 amSanta Rosa Sonoma County
6h 47m
1 stop
ORD7:21 pmChicago O'Hare Intl
Sep 14
ORD7:20 amChicago O'Hare Intl
18h 34m
1 stop
STS11:54 pmSanta Rosa Sonoma County
$367

momondo Fare Finder

 
Customize your flight search to find flights from Santa Rosa to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated August 9, 2026.
Use the filters below to find and compare flights from Santa Rosa to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Santa RosaChicago

STS Santa Rosa Sonoma County - ORD Chicago O'Hare Intl

STSORD

Santa Rosa Sonoma County

Sat 9/5

6:13 am-7:21 pm

1 stop11h 08m

Chicago O'Hare Intl

Fri 9/11

7:00 pm-12:46 pm

1 stop19h 46m

$299

Santa RosaChicago

STS Santa Rosa Sonoma County - ORD Chicago O'Hare Intl

STSORD

Santa Rosa Sonoma County

Sat 9/5

6:13 am-7:21 pm

1 stop11h 08m

Chicago O'Hare Intl

Fri 9/11

8:17 pm-9:54 am

1 stop15h 37m

$299

Santa RosaChicago

STS Santa Rosa Sonoma County - ORD Chicago O'Hare Intl

STSORD

Santa Rosa Sonoma County

Sat 9/5

6:16 am-7:21 pm

1 stop11h 05m

Chicago O'Hare Intl

Fri 9/11

8:17 pm-9:54 am

1 stop15h 37m

$299

Santa RosaChicago

STS Santa Rosa Sonoma County - ORD Chicago O'Hare Intl

STSORD

Santa Rosa Sonoma County

Fri 9/11

1:08 pm-12:30 am

1 stop9h 22m

Chicago O'Hare Intl

Mon 9/14

5:00 am-12:38 pm

1 stop9h 38m

$340

Santa RosaChicago

STS Santa Rosa Sonoma County - ORD Chicago O'Hare Intl

STSORD

Santa Rosa Sonoma County

Fri 9/11

1:08 pm-10:31 pm

1 stop7h 23m

Chicago O'Hare Intl

Wed 9/16

5:00 am-12:38 pm

1 stop9h 38m

$341

Santa RosaChicago

STS Santa Rosa Sonoma County - ORD Chicago O'Hare Intl

STSORD

Santa Rosa Sonoma County

Thu 9/10

1:08 pm-12:30 am

1 stop9h 22m

Chicago O'Hare Intl

Mon 9/14

5:00 am-12:09 pm

1 stop9h 09m

$345

Santa RosaChicago

STS Santa Rosa Sonoma County - ORD Chicago O'Hare Intl

STSORD

Santa Rosa Sonoma County

Sun 9/6

10:34 am-7:21 pm

1 stop6h 47m

Chicago O'Hare Intl

Wed 9/16

6:00 am-12:46 pm

1 stop8h 46m

$365
Quickest round-trip

Santa RosaChicago

STS Santa Rosa Sonoma County - ORD Chicago O'Hare Intl

STSORD

Santa Rosa Sonoma County

Sun 9/6

10:34 am-7:21 pm

1 stop6h 47m

Chicago O'Hare Intl

Sat 9/19

4:08 pm-9:59 pm

1 stop7h 51m

$365

Santa RosaChicago

STS Santa Rosa Sonoma County - ORD Chicago O'Hare Intl

STSORD

Santa Rosa Sonoma County

Wed 9/9

10:34 am-7:21 pm

1 stop6h 47m

Chicago O'Hare Intl

Fri 9/11

2:22 pm-8:59 pm

1 stop8h 37m

$365

Santa RosaChicago

STS Santa Rosa Sonoma County - ORD Chicago O'Hare Intl

STSORD

Santa Rosa Sonoma County

Sun 9/6

10:34 am-7:21 pm

1 stop6h 47m

Chicago O'Hare Intl

Tue 9/15

3:52 pm-9:59 pm

1 stop8h 07m

$365

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Santa Rosa to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the typical price of a round-trip flight between Santa Rosa and Chicago?

Prices are currently low for flights on this route.

Typical prices usually range from $400 to $500.
The lowest price recently found on this route was $299.

What is the cheapest month to fly to Chicago?

The month of January is, on average, the cheapest month to fly to Chicago from Santa Rosa, with most prices found around $0. If you’re not able to fly to Chicago in January, then November is your next best option. Flight prices from Santa Rosa to Chicago during November average around $315.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $443. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Santa Rosa to Chicago for around $576.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Santa Rosa to Chicago during this time can be as low as $470. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $510.

When to book flights from Santa Rosa to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Santa Rosa to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Santa Rosa to Chicago (STS to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Santa Rosa to Chicago

Fastest flight time

6h 47m

Direct flights

None
The fastest flight from Santa Rosa to Chicago takes 6h 47m
There are no direct flights from Santa Rosa to Chicago. There are no popular flight routes from Santa Rosa to Chicago.
Search flight deals

Frequently asked questions about flying from Santa Rosa to Chicago

  • How far is Santa Rosa Sonoma County to Chicago by plane?

    There are 1853.6 mi between Santa Rosa Sonoma County and Chicago. In terms of flight time, this usually takes a little over 6h 47m.

  • When did momondo last update prices for flights from Santa Rosa Sonoma County Airport to Chicago?

    Prices for flights from Santa Rosa Sonoma County Airport to Chicago refresh daily.

  • How many operators does momondo search for flights from Santa Rosa Sonoma County Airport to Chicago?

  • How old do you have to be to fly from Santa Rosa Sonoma County Airport to Chicago?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Santa Rosa Sonoma County Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular airline from Santa Rosa to Chicago?

Best airlines flying from Santa Rosa to Chicago

Compare and see reviews for airlines that fly from Santa Rosa to Chicago with momondo
Airline
Rating
Free Cancellation
Price
Alaska AirlinesPriceFrom $276Free CancellationRating
7.9
12,788 reviews
Search Alaska Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Santa Rosa to Chicago?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Santa Rosa to Chicago. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Santa Rosa to Chicago with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Chicago from Santa Rosa with this policy.

How can momondo help me find flights from Santa Rosa to Chicago?

momondo helps you find the best flight between Santa Rosa and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Santa Rosa to Chicago right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Santa Rosa to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport